Synthesis of N-Substituted Pyrido[b]-Anellated Azaphospholes

Content Provider	Scilit
Author	Kühl, O.
Editor	Adam, M. S. S. Kindermann, M. K. Heinicke, J. W. Jones, P. G.
Copyright Year	2008
Description	Reported are the first examples of the syntheses and structures of 3-amino and 3-amido pyridine-2-phosphonates, and the conversion of the latter heterocycles into azaphospholo[4,5-b]pyridines. After considerable testing of various conditions, the phosphonates were synthesized in low yields via Pd-catalyzed cross-coupling of bromopyridines with triethyl phosphite. The low yields were suggested to be due to the deactivating effects of the pyridine nitrogen and the amino group. Reduction of the amido phosphonates with $LiAlH_{4}$, followed by reaction with DMF dimethyl acetal led to the previously unknown P=C-N heterocycles in good yields. However, the compounds were found to be highly air-sensitive and their purification proved impossible in some cases.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2008-1078167.pdf
Ending Page	1025
Page Count	1
Starting Page	1025
ISSN	18611958
e-ISSN	1861194X
DOI	10.1055/s-2008-1078167
Journal	Synfacts
Issue Number	10
Volume Number	2008
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2008-09-22
Access Restriction	Open
Subject Keyword	Journal: Synfacts Organic Chemistry
Content Type	Text
Resource Type	Article